Oxidation of erythrose series sugars by sodium N-chlorobenzenesulphonamide in alkaline medium: A kinetic study

The kinetics of oxidation of D-glucose, D-mannose, D-fructose, D-arabinose, and D-ribose, with sodium N-chlorobenzenesulphonamide (chloramine-B or CAB) in alkaline medium have been studied at 35 degrees C and the rate law, rate = k' CAB] Sugar] OH-](2) is observed. The rate of reaction is influenced by a change in ionic strength of the medium, and the dielectric effect is negative. The solvent isotope studies in D2O show that the rate is almost doubled in heavy water. HPLC and GLC-MS analyses of the products indicated that the erythrose-series sugars are oxidized to a mixture of aldonic acids consisting of arabinonic, ribonic, erythronic, and glyceric acids in varying proportions. Based on these data, a mechanism involving the aldoenolic anions of pentoses and keto-enolic anions of hexoses is suggested